Because of age, wage or injury, he now gazes upon the diamond and sees his brethren drop like a baseball version of Whack-a-Mole. And whether it’s from the Steinbrenner family’s newfound frugality or a dearth of decent free agent talent this year, Jeter is staring at a dual sunset – the Yankees’ dynasty and his own dominance. As he limps onto the field for his 19th season, fresh off a broken ankle, not only is he facing Father Time (he turns 39 this season), but his own baseball mortality. No doubt he is asking the same question as his fans and fawning media: will Derek Jeter ever win another World Series? Will he even reach another World Series?

If we are indeed putting a postmortem on his postseason career, Jeter’s place is secured as the greatest everyday Yankee since Mickey Mantle. It’s fitting that Mike Francesa spent much of this afternoon pondering his place among Yankee immortals. The 20-something Yankees fans, who think the new, limestone martini bar is better than the old stadium, that baseball didn’t exist before 1996, all call Jeter the greatest Bronx Bomber of all-time, if not the greatest athlete of the last century. They’re the same folks who wear those nauseating “Got Rings?” t-shirts, spend seven innings on cell phones waving spastically at every camera within 100 feet, and wear jerseys with last names sewn on the back. We can’t reason with them.

Jeter has done the impossible. He has lived beyond his or our wildest dreams, cruised through a charmed life and enchanted career, yet he makes the masses feel sorry for him. Indeed, when I suggested two years ago, while he was thrashing inside the .260 swamp, that his best days were way behind him, I was called every vulgarity in the catalogue. In truth, no full-time shortstop in history has hit .300 after age 36. But I was a moron for suggesting that the same laws of batting and biology applied to Jeter. Turns out Jeter proved me wrong, but the notion that all stars and All-Stars age was (and still is) sound.

Jeter’s contract ends after this season (with a player option for 2014 at $8 million and a $3 million team buyout). And since fellow monoliths Mariano Rivera and Andy Pettitte are probably gone — definitely gone in Mo’s case — after 2013, Jeter could understandably consider following them. The Yankees fan’s ultimate nightmare is to see that holy trinity fail in their final seasons, and not get a last chance to wear long sleeves under brown leaves, their virtual birthright and eternal baseball visage.

Inexplicably, the Boss’ progeny let Russell Martin, Raul Ibanez and Rafael Soriano leave. And the moment it happened I said that letting Nick Swisher walk would haunt them. And now that fellow sluggers Curtis Granderson and Mark Teixeira are bitten by the injury bug, Brian Cashman is scrambling to find a new power source. Sadly, the stars aren’t aligned for a final playoff run. Depending on your source, the Bombers are slated to finish somewhere between second place and the bowels of the American League. For the first time in Jeter’s blessed career his team isn’t the chalk to walk through October.

And now the weight of the baseball world is pressing on Jeter’s aging, brittle bones. For a man whose handled the four-pronged pressure of playing pro baseball, in New York, for the Yankees, in the sport’s deadliest division (AL East) so well for so long, even Jeter must feel like the world is closing in on him. He may just decide to concede the throne in October, which could very well flip through the calendar without his bejeweled hands swinging a bat.

When you’ve been the king of New York for so long it will take a crane to rip the crown from his head. During his recent interview with Francesa, Jeter was audibly ornery when the subject of diminishing skills was broached. “Just because something hasn’t happened doesn’t mean it can’t happen,” is his template response to any question about remaining productive on the fringe of forty. Jeter was clearly defensive whenever age was wedged into the discussion. No doubt any player of his heft takes immeasurable pride in performance. And he’s also imbued with the hard-hat and hard-head ethics of an immortal player. Decay is a disease for the others, even if it isn’t.

But you must wonder what lies under the impenetrable platitudes he’s fed us for 18 years. To dance around the minefield of temptations, sycophants, groupies, is in itself a historic feat. But other than his two comrades from the glory years – Pettitte and Rivera, the landmarks of trademark Yankee dominance – Jeter must feel oddly out of place in this Yankee clubhouse. Gone are the requisite run producers that glittered up and down the Bronx Bombers’ lineup. So not only must Jeter fight his growing limitation and evaporating supporting cast, he must be as good as ever if the Yankees are to compete with Tampa, Baltimore, and newly-minted favorites in Toronto.

It’s a lot to ask, even if Jeter has answered nearly every prayer from a pampered fan base. One day Derek Jeter will wake up and not be able to stop, stab, and pirouette in the field. And the one-time rising star will one day whiff on a rising fastball. It will be a sad day in the Bronx. Andy Pettitte spoke wistfully about his sons, teaching them cutters and caginess. Mariano Rivera speaks in spiritual maxims. Though the two pitchers are clearly conflicted over leaving the sport they graced for so long, it’s obvious that Jeter is struggling the most with mortality. The fact that he hasn’t started a family is a vivid symbol of that struggle, as though he has no idea what do with his life once No. 2 is no longer No. 1.

We’ve seen splendid swan songs over the years, from John Elway to Jerome Bettis to Ray Lewis, whose resplendent careers ended with world championships. In each case the aging legend succumbed to age and surrendered to younger teammates. Jeter doesn’t have the luxury of the latter.

Thus it’s quite likely that Jeter won’t feel a Fall Classic under his feet again. And you need not be a Yankees fan to see how sad that is. You don’t have to feel sorry for Derek Jeter to hear the sorrow in a premature September Song for Mr. November.